(E,E)-Methyl 2-[(3-nitrobenzylidene)­aminomethyl]-3-phenylpropenoate

Bortoluzzi, A.J.; Bisol, T.B.; Sá, M.M.

doi:10.1107/S1600536808043262

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Pages o198-o199

doi:10.1107/S1600536808043262

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(E,E)-Methyl 2-[(3-nitrobenzylidene)aminomethyl]-3-phenylpropenoate

Adailton J. Bortoluzzi,^a ^* Tula B. Bisol ^a and Marcus M. Sá ^a

^aDepto. de Química - UFSC, 88040-900 - Florianópolis, SC, Brazil
^*Correspondence e-mail: adajb@qmc.ufsc.br

(Received 2 December 2008; accepted 19 December 2008; online 24 December 2008)

The molecule of the title compound, C₁₈H₁₆N₂O₄, adopts a T-shaped conformation with E stereochemistry for the imine double bond. The (3-nitrobenzylidene)amino fragment is almost planar, the mean planes of phenyl ring and nitro group forming a dihedral angle of 8.9 (3)°. In the 3-phenylacryloyl unit, the acrylic ester fragment is also almost planar, with the phenyl ring twisted by 41.44 (7)°. In the crystal, the molecules are linked by C—H⋯O hydrogen-bond interactions into chains running parallel to [01 $[\overline{1}]$ ].

Related literature

For general background to the chemistry of Morita–Baylis–Hillman adducts, see: Singh & Batra (2008 ); Masson et al. (2007 ); Basavaiah et al. (2003 ). For background to this study, see: Bortoluzzi et al. (2006 ); Fernandes et al. (2004 ); Sá et al. (2006 , 2007 , 2008 ). For the synthesis, see: Sá (2003 ). For a description of the Cambridge Structural Database, see: Allen (2002 ); and of MOGUL, see: Bruno et al. (2004 ).

Experimental

Crystal data

C₁₈H₁₆N₂O₄
M_r = 324.33
Triclinic, $[P \overline 1]$
a = 8.6035 (12) Å
b = 8.7829 (14) Å
c = 12.4680 (14) Å
α = 79.275 (18)°
β = 76.526 (13)°
γ = 63.158 (14)°
V = 813.9 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 (2) K
0.50 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
3026 measured reflections
2883 independent reflections
2165 reflections with > 2σ (I)
R_int = 0.024
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.124
S = 1.09
2883 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯O15ⁱ	0.93	2.55	3.307 (3)	139
Symmetry code: (i) x, y+1, z-1.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: SET4 in CAD-4 Software; data reduction: HELENA (Spek, 1996 ); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2003 ); Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808043262/rz2278sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808043262/rz2278Isup2.hkl

checkCIF report

Comment top

Nitrogen-containing building blocks derived from α-methylene-β-hydroxy esters (Morita-Baylis-Hillman adducts) have been widely employed in modern organic chemistry for the synthesis of natural products and heterocycles of biological relevance (Singh & Batra, 2008; Masson et al., 2007; Basavaiah et al., 2003). During our studies on the Morita-Baylis-Hillman reaction (Bortoluzzi et al., 2006; Fernandes et al., 2004; Sá et al., 2006; Sá et al., 2007; Sá et al., 2008), we reported the high-yield preparation of N-allylic imine (I) (Scheme 1) and analogs by a tandem Staudinger/Aza-Wittig process involving allyl azide (II) and a combination of triphenylphosphine and 3-nitrobenzaldehyde (Sá, 2003). In spite of the full chemical characterization described for the multifunctional compound (I), the stereochemistry of the imine double bond could not be unambiguously elucidated and was tentatively assigned as being E on the basis of the available data (Sá, 2003).

The molecular structure of the title compound adopts a T-shaped conformation (Fig. 1). The E stereochemistry for the imine double bond was unambiguously elucidated by X-ray analysis. The torsion angles N2—C1—C11—C12 of -8.2 (3)° and C12—C13—N13—O14 of 9.2 (3)° demonstrate that the (3-nitrobenzylidene)amino moiety is almost planar. The plane of the nitro group deviates of 8.9 (3)° with respect to the mean plane of the parent phenyl ring. In the 3-phenylacryloyl moiety, the acrylic ester fragment is also almost planar with as indicated by the C5–C4–C6–O7 torsion angle of 175.67 (18)°, whereas the phenyl ring is twisted by 41.44 (7)°, probably due to steric effect. This observation indicates that the vinyl C═C double bond is strongly conjugated with the carboxyl group instead that with the aromatic phenyl ring. A search using Mogul (Bruno et al., 2004) based on the CCDC system (version 5.29; Allen, 2002) revealed that the bond lengths found in the structure of (I) are within the expected range for organic compounds. In the crystal packing, molecules are linked by intermolecular C—H···O hydrogen bonding interactions (Table 1) to form chains running parallel to the [0 1 1] direction (Fig. 2).

Related literature top

For general background to the chemistry of Morita–Baylis–Hillman adducts, see: Singh & Batra (2008); Masson et al. (2007); Basavaiah et al. (2003). For background to this study, see: Bortoluzzi et al. (2006); Fernandes et al. (2004); Sá et al. (2006; 2007, 2008). For the synthesis, see:Sá (2003). For a description of the Cambridge Structural Database, see: Allen (2002); and of MOGUL, see: Bruno et al. (2004).

Experimental top

Allyl imine (I) was prepared as previously described (Sá, 2003). Allyl azide (II) and triphenylphosphine (1.0 mmol each) were stirred in anhydrous CHCl₃ (3.0 ml) and after evolution of N₂ has ceased, 3-nitrobenzaldehyde (1.0 mmol) was added and the mixture was stirred for further 20 h at room temperature. Concentration of the final mixture and separation of triphenylphosphine oxide by crystallization from ethyl ether furnished a white solid (84% yield). A careful recrystallization from ethyl acetate/hexane (1:3 v/v) provided crystals (mp 114.3–115.3 °C) suitable for X-ray crystallographic analysis.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: SET4 in CAD-4 Software (Enraf–Nonius, 1989); data reduction: HELENA (Spek, 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the labeling scheme. Displacement ellipsoids are shown at the 40% probability level.
	Fig. 2. Packing diagram of the title compound showing the formation of chains parallel to the [0 1 1] direction. Hydrogen bonds are shown as dashed lines.
	Fig. 3. Reaction scheme.

(E,E)-Methyl 2-[(3-nitrobenzylidene)aminomethyl]-3-phenylpropenoate top

Crystal data top

C₁₈H₁₆N₂O₄	Z = 2
M_r = 324.33	F(000) = 340
Triclinic, P1	D_x = 1.323 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.6035 (12) Å	Cell parameters from 25 reflections
b = 8.7829 (14) Å	θ = 5.3–16.7°
c = 12.4680 (14) Å	µ = 0.10 mm⁻¹
α = 79.275 (18)°	T = 293 K
β = 76.526 (13)°	Irregular block, colorless
γ = 63.158 (14)°	0.50 × 0.30 × 0.20 mm
V = 813.9 (2) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.024
Radiation source: fine-focus sealed tube	θ_max = 25.1°, θ_min = 1.7°
Graphite monochromator	h = −10→9
ω–2θ scans	k = −10→10
3026 measured reflections	l = −14→0
2883 independent reflections	3 standard reflections every 200 reflections
2165 reflections with > 2σ (I)	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0588P)² + 0.1527P] where P = (F_o² + 2F_c²)/3
2883 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₈H₁₆N₂O₄	γ = 63.158 (14)°
M_r = 324.33	V = 813.9 (2) Å³
Triclinic, P1	Z = 2
a = 8.6035 (12) Å	Mo Kα radiation
b = 8.7829 (14) Å	µ = 0.10 mm⁻¹
c = 12.4680 (14) Å	T = 293 K
α = 79.275 (18)°	0.50 × 0.30 × 0.20 mm
β = 76.526 (13)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.024
3026 measured reflections	3 standard reflections every 200 reflections
2883 independent reflections	intensity decay: 1%
2165 reflections with > 2σ (I)

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.09	Δρ_max = 0.17 e Å⁻³
2883 reflections	Δρ_min = −0.22 e Å⁻³
218 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.1755 (2)	0.5606 (2)	0.77725 (14)	0.0470 (4)
H1	0.1648	0.6615	0.7983	0.056*
N2	0.1722 (2)	0.55429 (18)	0.67793 (12)	0.0492 (4)
C3	0.1642 (3)	0.7065 (2)	0.60179 (15)	0.0514 (5)
H3A	0.2700	0.6741	0.5459	0.062*
H3B	0.1627	0.7908	0.6430	0.062*
C4	0.0043 (2)	0.7874 (2)	0.54518 (14)	0.0465 (4)
C5	0.0074 (2)	0.7661 (2)	0.44100 (14)	0.0488 (4)
H5	−0.0960	0.8330	0.4121	0.059*
C6	−0.1594 (3)	0.9030 (2)	0.61246 (15)	0.0515 (5)
O7	−0.1704 (2)	0.91839 (19)	0.70815 (11)	0.0734 (4)
O8	−0.29582 (18)	0.98968 (18)	0.55747 (11)	0.0639 (4)
C9	−0.4579 (3)	1.1040 (3)	0.6204 (2)	0.0796 (7)
H9A	−0.4923	1.0411	0.6855	0.119*
H9B	−0.5493	1.1532	0.5758	0.119*
H9C	−0.4398	1.1936	0.6416	0.119*
C11	0.1958 (2)	0.4135 (2)	0.86183 (14)	0.0446 (4)
C12	0.1900 (2)	0.2681 (2)	0.83818 (13)	0.0434 (4)
H12	0.1726	0.2610	0.7687	0.052*
C13	0.2104 (2)	0.1340 (2)	0.91989 (14)	0.0471 (4)
N13	0.2048 (2)	−0.01950 (19)	0.89347 (14)	0.0573 (4)
O14	0.2052 (2)	−0.03191 (17)	0.79774 (13)	0.0745 (5)
O15	0.2022 (3)	−0.13071 (19)	0.96882 (14)	0.0879 (5)
C14	0.2357 (3)	0.1386 (3)	1.02445 (15)	0.0579 (5)
H14	0.2487	0.0465	1.0780	0.069*
C15	0.2412 (3)	0.2832 (3)	1.04694 (16)	0.0625 (5)
H15	0.2582	0.2896	1.1166	0.075*
C16	0.2215 (3)	0.4193 (3)	0.96652 (15)	0.0555 (5)
H16	0.2255	0.5163	0.9829	0.067*
C21	0.1565 (2)	0.6482 (2)	0.36716 (14)	0.0465 (4)
C22	0.1946 (3)	0.7024 (2)	0.25635 (15)	0.0546 (5)
H22	0.1252	0.8133	0.2294	0.066*
C23	0.3330 (3)	0.5951 (3)	0.18584 (17)	0.0615 (5)
H23	0.3578	0.6345	0.1122	0.074*
C24	0.4353 (3)	0.4296 (3)	0.22366 (18)	0.0631 (5)
H24	0.5284	0.3567	0.1758	0.076*
C25	0.3986 (3)	0.3727 (3)	0.33283 (19)	0.0660 (6)
H25	0.4671	0.2607	0.3585	0.079*
C26	0.2610 (3)	0.4802 (2)	0.40479 (17)	0.0575 (5)
H26	0.2379	0.4405	0.4785	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0563 (11)	0.0396 (9)	0.0488 (10)	−0.0228 (8)	−0.0137 (8)	0.0000 (7)
N2	0.0628 (9)	0.0407 (8)	0.0475 (9)	−0.0251 (7)	−0.0172 (7)	0.0061 (6)
C3	0.0672 (12)	0.0433 (10)	0.0499 (10)	−0.0310 (9)	−0.0165 (9)	0.0089 (8)
C4	0.0590 (11)	0.0372 (9)	0.0456 (10)	−0.0253 (8)	−0.0114 (8)	0.0066 (7)
C5	0.0529 (10)	0.0424 (9)	0.0495 (10)	−0.0203 (8)	−0.0123 (8)	0.0039 (7)
C6	0.0668 (12)	0.0407 (9)	0.0452 (10)	−0.0263 (9)	−0.0070 (9)	0.0059 (8)
O7	0.0964 (11)	0.0643 (9)	0.0464 (8)	−0.0243 (8)	−0.0094 (7)	−0.0052 (7)
O8	0.0579 (8)	0.0640 (9)	0.0542 (8)	−0.0156 (7)	−0.0047 (6)	−0.0037 (6)
C9	0.0652 (14)	0.0729 (15)	0.0783 (16)	−0.0156 (12)	0.0041 (11)	−0.0130 (12)
C11	0.0488 (10)	0.0412 (9)	0.0426 (9)	−0.0192 (8)	−0.0077 (7)	−0.0012 (7)
C12	0.0486 (10)	0.0415 (9)	0.0377 (9)	−0.0174 (8)	−0.0083 (7)	−0.0019 (7)
C13	0.0512 (10)	0.0381 (9)	0.0462 (10)	−0.0161 (8)	−0.0066 (8)	−0.0008 (7)
N13	0.0659 (10)	0.0370 (8)	0.0624 (10)	−0.0180 (7)	−0.0122 (8)	0.0017 (7)
O14	0.1120 (13)	0.0471 (8)	0.0688 (10)	−0.0313 (8)	−0.0292 (9)	−0.0051 (7)
O15	0.1339 (15)	0.0511 (9)	0.0784 (11)	−0.0470 (10)	−0.0178 (10)	0.0146 (8)
C14	0.0723 (13)	0.0535 (11)	0.0439 (10)	−0.0271 (10)	−0.0127 (9)	0.0088 (8)
C15	0.0845 (15)	0.0690 (13)	0.0398 (10)	−0.0371 (11)	−0.0171 (10)	0.0012 (9)
C16	0.0724 (13)	0.0543 (11)	0.0467 (10)	−0.0325 (10)	−0.0109 (9)	−0.0047 (8)
C21	0.0509 (10)	0.0436 (9)	0.0493 (10)	−0.0228 (8)	−0.0130 (8)	−0.0018 (8)
C22	0.0623 (12)	0.0505 (11)	0.0479 (10)	−0.0202 (9)	−0.0164 (9)	0.0015 (8)
C23	0.0650 (12)	0.0672 (13)	0.0484 (11)	−0.0253 (11)	−0.0078 (9)	−0.0065 (9)
C24	0.0579 (12)	0.0596 (12)	0.0693 (14)	−0.0199 (10)	−0.0076 (10)	−0.0179 (10)
C25	0.0702 (13)	0.0401 (10)	0.0814 (15)	−0.0167 (10)	−0.0171 (11)	−0.0040 (10)
C26	0.0683 (12)	0.0432 (10)	0.0593 (12)	−0.0253 (9)	−0.0111 (9)	0.0034 (8)

Geometric parameters (Å, º) top

C1—N2	1.257 (2)	C13—C14	1.381 (3)
C1—C11	1.478 (2)	C13—N13	1.470 (2)
C1—H1	0.9300	N13—O14	1.218 (2)
N2—C3	1.473 (2)	N13—O15	1.227 (2)
C3—C4	1.509 (2)	C14—C15	1.373 (3)
C3—H3A	0.9700	C14—H14	0.9300
C3—H3B	0.9700	C15—C16	1.383 (3)
C4—C5	1.339 (2)	C15—H15	0.9300
C4—C6	1.481 (3)	C16—H16	0.9300
C5—C21	1.473 (2)	C21—C22	1.389 (3)
C5—H5	0.9300	C21—C26	1.395 (3)
C6—O7	1.203 (2)	C22—C23	1.373 (3)
C6—O8	1.342 (2)	C22—H22	0.9300
O8—C9	1.445 (2)	C23—C24	1.376 (3)
C9—H9A	0.9600	C23—H23	0.9300
C9—H9B	0.9600	C24—C25	1.375 (3)
C9—H9C	0.9600	C24—H24	0.9300
C11—C16	1.387 (2)	C25—C26	1.382 (3)
C11—C12	1.388 (2)	C25—H25	0.9300
C12—C13	1.380 (2)	C26—H26	0.9300
C12—H12	0.9300

N2—C1—C11	122.48 (16)	C12—C13—N13	118.04 (16)
N2—C1—H1	118.8	C14—C13—N13	119.12 (16)
C11—C1—H1	118.8	O14—N13—O15	122.86 (17)
C1—N2—C3	116.16 (15)	O14—N13—C13	118.70 (15)
N2—C3—C4	113.24 (14)	O15—N13—C13	118.44 (17)
N2—C3—H3A	108.9	C15—C14—C13	118.01 (17)
C4—C3—H3A	108.9	C15—C14—H14	121.0
N2—C3—H3B	108.9	C13—C14—H14	121.0
C4—C3—H3B	108.9	C14—C15—C16	120.37 (18)
H3A—C3—H3B	107.7	C14—C15—H15	119.8
C5—C4—C6	121.26 (17)	C16—C15—H15	119.8
C5—C4—C3	124.23 (17)	C15—C16—C11	121.17 (18)
C6—C4—C3	114.43 (16)	C15—C16—H16	119.4
C4—C5—C21	127.15 (17)	C11—C16—H16	119.4
C4—C5—H5	116.4	C22—C21—C26	118.14 (17)
C21—C5—H5	116.4	C22—C21—C5	120.03 (16)
O7—C6—O8	122.52 (18)	C26—C21—C5	121.82 (16)
O7—C6—C4	123.31 (18)	C23—C22—C21	121.17 (18)
O8—C6—C4	114.17 (16)	C23—C22—H22	119.4
C6—O8—C9	115.78 (16)	C21—C22—H22	119.4
O8—C9—H9A	109.5	C22—C23—C24	120.28 (19)
O8—C9—H9B	109.5	C22—C23—H23	119.9
H9A—C9—H9B	109.5	C24—C23—H23	119.9
O8—C9—H9C	109.5	C25—C24—C23	119.5 (2)
H9A—C9—H9C	109.5	C25—C24—H24	120.3
H9B—C9—H9C	109.5	C23—C24—H24	120.3
C16—C11—C12	118.96 (16)	C24—C25—C26	120.70 (19)
C16—C11—C1	120.11 (16)	C24—C25—H25	119.7
C12—C11—C1	120.93 (15)	C26—C25—H25	119.7
C13—C12—C11	118.65 (16)	C25—C26—C21	120.21 (19)
C13—C12—H12	120.7	C25—C26—H26	119.9
C11—C12—H12	120.7	C21—C26—H26	119.9
C12—C13—C14	122.84 (17)

C11—C1—N2—C3	−175.74 (16)	C14—C13—N13—O14	−170.73 (18)
C1—N2—C3—C4	−121.34 (18)	C12—C13—N13—O15	−171.67 (17)
N2—C3—C4—C5	−101.1 (2)	C14—C13—N13—O15	8.4 (3)
N2—C3—C4—C6	82.07 (19)	C12—C13—C14—C15	−0.2 (3)
C6—C4—C5—C21	−175.96 (15)	N13—C13—C14—C15	179.74 (18)
C3—C4—C5—C21	7.5 (3)	C13—C14—C15—C16	0.1 (3)
C5—C4—C6—O7	175.67 (18)	C14—C15—C16—C11	0.0 (3)
C3—C4—C6—O7	−7.4 (2)	C12—C11—C16—C15	0.0 (3)
C5—C4—C6—O8	−4.2 (2)	C1—C11—C16—C15	−179.85 (18)
C3—C4—C6—O8	172.71 (14)	C4—C5—C21—C22	−138.14 (19)
O7—C6—O8—C9	0.2 (3)	C4—C5—C21—C26	42.9 (3)
C4—C6—O8—C9	−179.94 (16)	C26—C21—C22—C23	−1.1 (3)
N2—C1—C11—C16	171.68 (18)	C5—C21—C22—C23	179.90 (17)
N2—C1—C11—C12	−8.2 (3)	C21—C22—C23—C24	1.2 (3)
C16—C11—C12—C13	−0.1 (3)	C22—C23—C24—C25	−0.5 (3)
C1—C11—C12—C13	179.71 (16)	C23—C24—C25—C26	−0.3 (3)
C11—C12—C13—C14	0.3 (3)	C24—C25—C26—C21	0.4 (3)
C11—C12—C13—N13	−179.70 (15)	C22—C21—C26—C25	0.3 (3)
C12—C13—N13—O14	9.2 (3)	C5—C21—C26—C25	179.29 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O15ⁱ	0.93	2.55	3.307 (3)	139

Symmetry code: (i) x, y+1, z−1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₂O₄
M_r	324.33
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.6035 (12), 8.7829 (14), 12.4680 (14)
α, β, γ (°)	79.275 (18), 76.526 (13), 63.158 (14)
V (Å³)	813.9 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.50 × 0.30 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [ > 2σ (I)] reflections	3026, 2883, 2165
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.124, 1.09
No. of reflections	2883
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.22

Computer programs: , SET4 in CAD-4 Software (Enraf–Nonius, 1989), HELENA (Spek, 1996), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003); Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O15ⁱ	0.93	2.55	3.307 (3)	139.0

Symmetry code: (i) x, y+1, z−1.

Acknowledgements

The authors are grateful to the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) and the Fundação de Apoio à Pesquisa Científica e Tecnológica do Estado de Santa Catarina (FAPESC) for financial assistance.

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